EP4635273A1 - Dispositif électroluminescent organique comprenant un composé de formule (i) et un composé de formule (ii), et dispositif d'affichage comprenant le dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique comprenant un composé de formule (i) et un composé de formule (ii), et dispositif d'affichage comprenant le dispositif électroluminescent organique

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Publication number
EP4635273A1
EP4635273A1 EP23828126.5A EP23828126A EP4635273A1 EP 4635273 A1 EP4635273 A1 EP 4635273A1 EP 23828126 A EP23828126 A EP 23828126A EP 4635273 A1 EP4635273 A1 EP 4635273A1
Authority
EP
European Patent Office
Prior art keywords
substituted
group
unsubstituted
alkyl
perfluorinated
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP23828126.5A
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German (de)
English (en)
Inventor
Vladimir UVAROV
Piermaria PINTER
Regina LUSCHTINETZ
Thomas Rosenow
Peter Robaschik
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NovaLED GmbH
Original Assignee
NovaLED GmbH
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Filing date
Publication date
Application filed by NovaLED GmbH filed Critical NovaLED GmbH
Publication of EP4635273A1 publication Critical patent/EP4635273A1/fr
Pending legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/19—Tandem OLEDs
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/331—Metal complexes comprising an iron-series metal, e.g. Fe, Co, Ni
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight

Definitions

  • Organic electroluminescent device comprising a compound of formula (I) and a compound of formula (II), and display device comprising the organic electroluminescent device
  • the present invention relates to an electroluminescent device comprising a compound of formula (I) and a compound of formula (II), and a display device comprising the organic electroluminescent device.
  • Organic electronic devices such as organic light-emitting diodes OLEDs, which are self- emitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction.
  • a typical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate.
  • the HTL, the EML, and the ETL are thin films formed from organic compounds.
  • Performance of an organic light emitting diode may be affected by characteristics of the semiconductor layers, and among them, may be affected by characteristics of the compounds contained in the semiconductor layers.
  • An aspect of the present invention provides organic electroluminescent device comprising an anode layer, a cathode layer, a first emission layer, a second emission layer, a hole injection layer, and a first charge generation layer, wherein the hole injection layer is in direct contact to the anode layer; wherein the first charge generation layer is arranged between the first emission layer and the second emission layer; wherein the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer; wherein the first n-type charge generation layer is closer to the anode layer than the first p-type charge generation layer; wherein the n-type charge generation layer comprises a metal dopant and a matrix compound, wherein the first p-type charge generation layer comprises a second hole transport matrix compound and a compound of formula (I);
  • a 1 is independently selected from a group of formula (la) wherein Ar 1 is independently selected from substituted or unsubstituted C6 to
  • a 2 is independently selected from a group of formula (lb)
  • Ar 2 is independently selected from substituted or unsubstituted C6 to C36 aryl, and substituted or unsubstituted C2 to C36 heteroaryl; wherein for the case that Ar 2 is substituted, one or more of the substituents are independently selected from the group consisting of D, an electron- withdrawing group, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted C6 to C30 aryl, and substituted or unsubstituted C6 to C30 heteroaryl and; wherein the one or more substituents of C6 to C30 aryl, C6 to C
  • a 3 is independently selected from a group of formula (Ic)
  • Ar 3 is independently selected from substituted or unsubstituted C6 to C36 aryl, and substituted or unsubstituted C2 to C36 heteroaryl; wherein for the case that Ar 3 is substituted, one or more of the substituents are independently selected from the group consisting of D, an electron- withdrawing group, halogen, Cl, F, CN, -NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C8 alkoxy, substituted or unsubstituted Ce to C30 aryl, and substituted or unsubstituted C6 to C30 heteroaryl and; wherein the one or more substituents of C6 to C30 aryl, C6 to C30 aryl, C
  • aryl substituted refers to a substitution with one or more aryl groups, which themselves may be substituted with one or more aryl and/or heteroaryl groups.
  • heteroaryl substituted refers to a substitution with one or more heteroaryl groups, which themselves may be substituted with one or more aryl and/or heteroaryl groups.
  • an "alkyl group” refers to a saturated aliphatic hydrocarbyl group.
  • the alkyl group may be a C1 to C12 alkyl group. More specifically, the alkyl group may be a C1 to C10 alkyl group or a C1 to C6 alkyl group.
  • a C1 to C4 alkyl group includes 1 to 4 carbons in alkyl chain, and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl.
  • alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group.
  • cycloalkyl refers to saturated hydrocarbyl groups derived from a cycloalkane by formal abstraction of one hydrogen atom from a ring atom comprised in the corresponding cycloalkane.
  • examples of the cycloalkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantly group and the like.
  • hetero is understood the way that at least one carbon atom, in a structure which may be formed by covalently bound carbon atoms, is replaced by another polyvalent atom.
  • the heteroatoms are selected from B, Si, N, P, O, S; more preferably from N, P, O, S.
  • aryl group refers to a hydrocarbyl group which can be created by formal abstraction of one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon.
  • Aromatic hydrocarbon refers to a hydrocarbon which contains at least one aromatic ring or aromatic ring system.
  • Aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons fulfilling Htickel’s rule.
  • aryl groups include monocyclic groups like phenyl or tolyl, polycyclic groups which comprise more aromatic rings linked by single bonds, like biphenyl, and polycyclic groups comprising fused rings, like naphtyl or fluoren-2-yl.
  • heteroaryl it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a heterocyclic aromatic ring in a compound comprising at least one such ring.
  • heterocycloalkyl it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a saturated cycloalkyl ring in a compound comprising at least one such ring.
  • fused aryl rings or “condensed aryl rings” is understood the way that two aryl rings are considered fused or condensed when they share at least two common sp 2 -hybridized carbon atoms.
  • cyano moiety refers to a CN substituent.
  • electron-withdrawing group refers to a chemical group in a molecule, which can draw electrons away from an adjacent part of the molecule.
  • the distance over which the electron- withdrawing group can exert its effect, namely the number of bonds over which the electron-withdrawing effect spans, is extended by conjugated pi-electron systems such as aromatic systems.
  • electron-withdrawing groups include NO2, CN, halogen, Cl, F, partially fluorinated or perfluorinated alkyl and partially fluorinated or perfluorinated C1 to C12 alkyl, partially fluorinated or perfluorinated alkoxy, partially fluorinated or perfluorinated C1 to Ce alkoxy.
  • the single bond refers to a direct bond.
  • n-type charge generation layer is sometimes in the art also named n-CGL or electron generation layer and is intended to include the both.
  • p-type charge generation layer is sometimes in the art also named p-CGL or hole generation layer and is intended to include the both.
  • contacting sandwiched refers to an arrangement of three layers whereby the layer in the middle is in direct contact with the two adjacent layers.
  • light-absorbing layer and “light absorption layer” are used synonymously.
  • light-emitting layer and “light emission layer” are used synonymously.
  • OLED organic light-emitting diode
  • organic light-emitting device organic light-emitting device
  • anode anode layer and “anode electrode” are used synonymously.
  • cathode cathode layer
  • cathode electrode cathode electrode
  • top emission device is understood to mean an organic electronic device wherein the light is emitted through the cathode layer.
  • bottom emission device is understood to mean an organic electronic device wherein the light is emitted through the substrate.
  • hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied and that a hole formed in the anode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a highest occupied molecular orbital (HOMO) level.
  • HOMO highest occupied molecular orbital
  • electron characteristics refer to an ability to accept an electron when an electric field is applied and that electrons formed in the cathode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a lowest unoccupied molecular orbital (LUMO) level.
  • LUMO lowest unoccupied molecular orbital
  • the organic electroluminescent device according to the invention solves the problem underlying the present invention by enabling devices in various aspects superior over the organic electroluminescent devices known in the art, in particular with respect to improved operating voltage, improved operating voltage stability over time and improved current efficiency.
  • the compound of formula (I) has a calculated LUMO energy level, expressed in the absolute scale referring to vacuum energy level being zero, of ⁇ -4.90 eV, preferabl ⁇ y -5.00 eV, more preferabl ⁇ y -5.05 eV, and most preferably ⁇ -5.10 eV, when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the compound of formula (I) has a calculated LUMO energy level, expressed in the absolute scale referring to vacuum energy level being zero, in the range of ⁇ -4.90 eV to ⁇ -5.75 eV, preferabl ⁇ y -5.00 eV to ⁇ -5.75 eV, more preferabl ⁇ y -5.05 eV to ⁇ -5.75 eV and most preferabl ⁇ y -5.10 eV to ⁇ -5.75 eV, when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the compound of formula (I) is present in the p-type charge generation layer in an amount of ⁇ 1 wt% and ⁇ 20 wt% based on the total weight of the p-type charge generation layer, preferably ⁇ 5 wt% and ⁇ 10 wt%.
  • the compound of formula (I) is an organic p-dopant.
  • the following compounds are excluded: 4,4',4"-((lE,l'E,l”E)-cyclopropane-l,2,3- triylidenetris(cyanomethanylylidene))tris(2,3,5,6-tetrafluorobenzonitrile); (2E,2'E,2"E)-2,2',2"- (cyclopropane-l,2,3-triylidene)tris(2-(2,6-dichloro-3,5-difluoro-4-(trifluoromethyl)phenyl)- acetonitrile); ⁇ , ⁇ ', ⁇ "-l,2,3-Cyclopropanetriylidenetris[2,3,4,5,6-pentafluorobenzeneacetonitrile]; and ⁇ , ⁇ ', ⁇ "-l,2,3-Cyclopropanetriylidenetris[2,3,5,6-tetrafluor
  • the compound of formula (I) comprises at least one CF3 group.
  • the compound of formula (I) comprises at one to three CF3 group.
  • the compound of formula (I) comprises less than nine cyano moieties.
  • the compound of formula (I) comprises less than eight cyano moieties.
  • the compound of formula (I) comprises at least one cyano moiety.
  • the compound of formula (I) comprises at least two cyano moieties. According to one embodiment of the present invention, the compound of formula (I) comprises at least three cyano moieties.
  • the compound of formula (I) comprises at least four cyano moieties.
  • the compound of formula (I) comprises from 3 to 8 cyano moieties.
  • the compound of formula (I) comprises from 3 to 7 cyano moieties.
  • the compound of formula (I) comprises from 4 to 7 cyano moieties.
  • formula (I) comprises at least 10 fluorine atoms, at least 12 fluorine atoms, at least 13 fluorine atoms, 14 at least fluorine atoms, at least 15 fluorine atoms, at least 16 fluorine atoms, at least 17 fluorine atoms, or at least 18 fluorine atoms.
  • formula (I) comprises 10 to 20 fluorine atoms, or 10 to 18 fluorine atoms or 12 to 18 fluorine atoms.
  • formula (I) comprises 4 to 7 cyano moieties and 12 to 18 fluorine atoms.
  • At least two of A 1 , A 2 , and A 3 are selected the same.
  • a 2 and A 3 are identical.
  • a 1 , A 2 and A 3 are identical.
  • a 1 is different from A 2 and/or A 3 .
  • Ar 1 , Ar 2 , and Ar 3 are independently selected from substituted or unsubstituted C6 to C12 aryl and substituted or unsubstituted C3 to C12 heteroaryl.
  • Ar 1 , Ar 2 , and Ar 3 are independently selected from substituted or unsubstituted C6 aryl and substituted or unsubstituted C3 to C5 heteroaryl.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of an electron- withdrawing group, halogen, Cl, F, CN, partially fluorinated alkyl, and perfluorinated alkyl.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of Cl, F, CN, and perfluorinated alkyl.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of F, CN, and perfluorinated alkyl.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of F, CN, and CF3.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of CN, and CF3.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of CN.
  • the substituents on Ar 1 , Ar 2 , and Ar 3 are independently selected from the group consisting of CF3.
  • Ar 1 , Ar 2 , and Ar 3 independently each comprise more than one and less than five substituents, preferably more than two and less than four, for example 4.
  • each R’ is independently selected from electron- withdrawing group, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN.
  • each R’ is independently selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, halogen, F and CN.
  • each R’ is independently selected from CF3, F and CN.
  • each R’ is CN.
  • Ar 1 , Ar 2 and Ar 3 are independently selected from a group according to the following formula (III) and preferably each R’ is selected from CN: wherein
  • E 1 is selected from CW 1 or N;
  • E 2 is selected from CW 2 or N;
  • E 3 is selected from CW 3 or N;
  • E 4 is selected from CW 4 or N;
  • E 5 is selected from CW 5 or N;
  • W 1 , W 2 , W 3 , W 4 and W 5 are independently selected from electron- withdrawing group, CN, halogen, Cl, F, NO2, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, substituted or unsubstituted C1 to C8 alkoxy, partially fluorinated C1 to C8 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C3 to C30 heteroaryl, D or H, wherein the one or more substituents is independently selected from D, halogen, Cl, F, CN, NO2, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, partially fluorinated C1 to C8 alkoxy, perfluorinated C
  • W 1 , W 2 , W 3 , W 4 and W 5 are independently selected from electron-withdrawing group, CN, halogen, Cl, F, NO2, partially fluorinated or perfluorinated C1 to C8 alkyl, partially fluorinated or perfluorinated C1 to C6 alkoxy, D or H, and wherein preferably each R’ is selected from CN.
  • Ar 1 , Ar 2 and Ar 3 are independently selected from Bl to B64 and preferably each R’ is selected from CN:
  • Ar 1 , or Ar 1 , Ar 2 and Ar 3 and/or in the are independently selected from one of the following groups of Bl to B 8, BIO to B17, Bl 9 to B21, B24 to B26, B33, B34, B37, B40, B43, B58 to B62 and B64, and preferably in the compound of formula (I) Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups of B2, B3, B4, Bl l, Bl 3, B37, B43, B58, B59, B60, B61, B63 and B64.
  • Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups of Bl to B64, and wherein preferably each R’ and/or R” are selected from CN, and preferably wherein in the compound of formula (I) Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups of Bl to B5, B7, B8, BIO to B13, B15 to B17, B19 to B21, B37, B43, B58 to B61, B63 and B64 and wherein preferably each R’ and/or R” are selected from CN.
  • Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups:
  • each R’ and/or R” is selected from CN.
  • Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups: wherein the asterisk denotes the binding position; and wherein preferably each R’ and/or R” is selected from CN.
  • Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups:
  • Ar 1 , or Ar 1 , Ar 2 and Ar 3 are independently selected from one of the following groups: wherein the asterisk denotes the binding position; and wherein each R’ is selected from CN.
  • the compound of formula (I) is selected from one of the following compounds BRI to BR14, wherein R’ is selected from CN and Ar 1 of A 1 , Ar 2 of A 2 , and Ar 3 of A 3 are selected as follows:
  • the compound of formula (I) is selected from one of the following compounds BR2 to BR6, wherein R’ is selected from CN and Ar 1 of A 1 , Ar 2 of A 2 , and Ar 3 of A 3 are selected as follows: wherein the asterisk denotes the binding position.
  • the compound of formula (I) is represented by one of the following formulae (Illa) to (Illh): (nid) (Illh) wherein Ar 1 , Ar 2 , Ar 3 , and R’ are independently selected as above.
  • the hole injection layer comprises as compound of formula (I) a mixture of at least two compounds selected from formulae (Illa) to (Illh) as defined above.
  • the compound of formula (II) has a LUMO energy level of ⁇ -7.0 eV to ⁇ -1.5 eV whereby the calculations are performed by applying the hybrid functional B3LYP with the Def2-TZVP basis set with the SDD Effective Core Potentials (ECPs) for the metals, in the gas phase as implemented in the program package ORCA Version 5.0.3-f.l (Department of Theory and Spectroscopy, Max Planck Institute fur Kohlenforschung Kaiser Wilhelm Platz 1, 45470 Muelheim/Ruhr, Germany).
  • compound of formula (II) has a LUMO energy level of ⁇ -6.5 eV to ⁇ - 1.7 eV, or ⁇ -6.0 eV to ⁇ -2.0 eV, or ⁇ -5.9 eV to ⁇ -2.3 eV; or ⁇ -5.8 eV to ⁇ -2.7 eV; or ⁇ -5.7 eV to ⁇ -3.9 eV or ⁇ -5.6 eV to ⁇ -4.2 eV; or preferred ⁇ -5.5 eV to ⁇ -4.3 eV.
  • the compound of formula (II) comprises a metal cation selected from Ce, Cu, Ag, alkali metal, alkaline earth metal, Bi, Al, Ga, In; Zr, Hf, Cr, and/or Fe.
  • the compound of formula (II) comprises a metal cation selected from Ce, Cu, Ag, Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Bi, In and/or Fe, preferably Ce(IV), Cu(II), Ag(I), Li(I), Na(I), K(I), Rb(I), Cs(I), Be(II), Mg(II), Ca(II), Sr(II), Ba(II), Bi(III), In(III), Cr(III) and/or Fe(III).
  • a metal cation selected from Ce, Cu, Ag, Li, Na, K, Rb, Cs, Be, Mg, Ca, Sr, Ba, Bi, In and/or Fe, preferably Ce(IV), Cu(II), Ag(I), Li(I), Na(I), K(I), Rb(I), Cs(I), Be(II), Mg(II), Ca(II), Sr(II), Ba(II), Bi(III),
  • the compound of formula (II) comprises a metal cation selected from Ce, Cu, Ag, Na, Cs, Bi, and/or Fe, preferably Ce(IV), Cu(II), Ag(I), Na(I), Cs(I), Bi(III); Cr(III) and/or Fe(III).
  • the compound of formula (II) is comprises a metal cation selected from Ce, Cu and/or Fe preferably Ce(IV), Cu(II), and/or Fe(III).
  • the compound of formula (II) is a metal complex.
  • compound of formula (II) is metal complex comprising a metal cation selected from Ce, Cu and/or Fe preferably Ce(IV), Cu(II), and/or Fe(III).
  • compound of formula (II) is metal complex having a LUMO energy level of ⁇ -7.00 eV to ⁇ -1.50 eV whereby the calculations are performed by applying the hybrid functional B3LYP with the Def2-TZVP basis set with the SDD Effective Core Potentials (ECPs) for the metals, in the gas phase as implemented in the program package ORCA Version 5.0.3-f.1 (Department of Theory and Spectroscopy, Max Planck Institute fur Kohlenforschung Kaiser Wilhelm Platz 1, 45470 Muelheim/Ruhr, Germany) wherein the metal complex comprises a metal cation selected from Ce, Fe, and/or Cu preferably Ce(IV), Cu(II), and/or Fe(III).
  • compound of formula (II) comprises at least one CF3 group.
  • compound of formula (II) comprises at least one CF3 group which is not bound to an oxygen.
  • the compound of formula (II) comprises at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms, wherein the monoanion or the monoanionic ligand is presented by L' according to formula (IV) or compound of formula (II) is represented by formula (na)
  • Z is selected from CR 1 , C, O, N, B; if Z is selected O then n, p, q and are selected from 0 and s, t and u are selected from 0; if Z is selected from N or CR 1 then p and q are selected from 0, and t and u are selected from 0; if Z is selected from C then q is selected from 0, and u is selected from 0; if Z is selected from B then n, m, p, and q are selected from 1, and r, s, t, and u are selected from 1 ;
  • R 1 is selected from H, D, electron-withdrawing group, halogen, Cl, F, CN, NO2, SF5, isonitrile, ester group, carboxylic group, carbonyl group, acyl group, thio group sulfinyl group, sulfonyl group, phosphine group, substituted or unsubstituted C1 to C12 alkyl, partially perfluorinated C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, CF3, substituted or unsubstituted C1 to C12 alkoxy, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, CF3, substituted or unsubstituted C6 to C40 aryl, substituted or unsubstituted C2 to C40 heteroaryl, substituted or unsubstituted C3 to C30, carbocyclyl, substituted or unsubstituted C3 to
  • R 2 , R 3 and R 4 are independently selected from H, D, electron-withdrawing group, halogen, Cl, F, CN, ester group, carboxylic group, carbonyl group, acyl group, thio group sulfinyl group, sulfonyl group, phosphine group, substituted or unsubstituted alkyl, partially perfluorinated C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, CF3, substituted or unsubstituted C1 to C6 alkoxy, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, substituted or unsubstituted C6 to C40 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted C3 to C30 carbocyclyl, substituted or unsubstituted C2 to C30 heterocyclyl, where
  • none R a R b , R c and R d is substituted or unsubstituted C3 to C40 carbocyclyl.
  • Ancillary ligands are defined as those ligands that provide the appropriate steric and electronic environment around the central element but remain innocent in any transformation that the compound undergoes.
  • reactive ligands are those groups that undergo changes.
  • AL is selected from the group comprising H2O, C2 to C40 mono- or multi-dentate ethers and C2 to C40 thioethers, C2 to C40 amines, C2 to C40 phosphine, C2 to C20 alkyl nitrile or C2 to C40 aryl nitrile, or a compound according to Formula (AL-I); wherein
  • R 6 and R 7 are independently selected from C1 to C20 alkyl, C1 to C20 heteroalkyl, C6 to C20 aryl, heteroaryl with 5 to 20 ring-forming atoms, halogenated or perhalogenated C1 to C20 alkyl, halogenated or perhalogenated C1 to C20 heteroalkyl, halogenated or perhalogenated C6 to C20 aryl, halogenated or perhalogenated heteroaryl with 5 to 20 ring-forming atoms, or at least one R 6 and R 7 are bridged and form a 5 to 20 member ring, or the two R 6 and/or the two R 7 are bridged and form a 5 to 40 member ring or form a 5 to 40 member ring comprising an unsubstituted or C1 to C12 substituted phenanthroline.
  • Z can form a double bond to A 1 , A 2 , A 3 and A 4 , if A 1 , A 2 , A 3 and A 4 is selected from C-0 or C-NR 3 and Z is selected from N, O or CR 1 , or A 1 , A 2 , A 3 and A 4 is selected from C-0 or C-NR 3 and Z is selected from C ; and wherein optionally two of A 1 , A 2 , A 3 and A 4 together can form a substituted or unsubstituted heterocycle or substituted or unsubstituted carbocycle with Z, or wherein optionally one of A 1 , A 2 , A 3 and A 4 can form a substituted or unsubstituted heterocycle or substituted or unsubstituted carbocycle with Z, wherein the one or more substituent on the heterocycle or carbocycle is independently selected from D, electron-withdrawing group, halogen, F, CN, NO2, SF5, partially
  • R 1 is selected from CN, substituted or unsubstituted C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, or CF3.
  • R 1 is selected from CN, or substituted or unsubstituted C1 to C12 alkyl.
  • R a R b , R c and R d are independently selected from H, D, electron-withdrawing group, halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C3 to C12 heteroaryl, substituted or unsubstituted C3 to C 12 heterocyclyl, O, S, N, NR 5 , substituted or unsubstituted amine group having 0 to 20 carbon atoms; wherein the one more substituents on R a , R b , R c and R d are independently selected from electron-withdrawing group, halogen, F, CN, NO2, SF5, partially perfluorinated C1 to C6 alkyl,
  • R 2 , R 3 and R 4 are independently selected from substituted or unsubstituted alkyl, partially perfluorinated C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, CF3, substituted or unsubstituted C1 to C6 alkoxy, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, substituted or unsubstituted C6 to C40 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted C3 to C30 carbocyclyl, substituted or unsubstituted C2 to C30 heterocyclyl, wherein the substituents on R 2 , R 3 and R 4 are independently selected from D, F, CN, NO2, SF5.
  • R 1 is selected from CN, substituted or unsubstituted C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, or CF3;
  • R 2 , R 3 and R 4 are independently selected from substituted or unsubstituted alkyl, partially perfluorinated C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, CF3, substituted or unsubstituted C1 to C6 alkoxy, partially perfluorinated C1 to C6 alkoxy, perfluorinated C1 to C6 alkoxy, OCF3, substituted or unsubstituted C6 to C40 aryl, substituted or unsubstituted C2 to C30 heteroaryl, substituted or unsubstituted C3 to C30 carbocyclyl, substituted or unsubstituted C2 to C30 heterocyclyl, wherein the substituents on R 2 , R 3 and R 4 are independently selected from D, F, CN, NO2, SF5;
  • R a R b , R c and R d are independently selected from H, D, electron-withdrawing group, halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkyl, CF3, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C3 to C12 heteroaryl, substituted or unsubstituted C3 to C12 heterocyclyl, O, S, N, NR 5 , substituted or unsubstituted amine group having 0 to 20 carbon atoms; wherein the one more substituents on R a , R b , R c and R d are independently selected from electron-withdrawing group, halogen, F, CN, NO2, SF5, partially perfluorinated C1 to C6 alkyl, perfluorinated C1 to C
  • the monoanion or the monoanionic ligand L' is selected from (V), (VI), (VII), (VIII) or (IX)
  • R a are independently selected from substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, or substituted or unsubstituted 6-membered heteroaryl;
  • R b is selected from substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to C19 aryl, substituted or unsubstituted C2 to C20 heteroaryl, substituted or unsubstituted 6-membered heteroaryl, or CN; wherein at least one of the substituents of the substituted C1 to C12 alkyl, substituted C6 to C19 aryl, substituted C2 to C20 heteroaryl, or substituted 6-membered heteroaryl are independently selected from halogen, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl, partially or perfluorinated C1 to C8 alkoxy; wherein in formula (VI) at least one of R a , R b and R a or the group of R a , R b and R a comprises at least three atoms selected from the group consisting of halogen, Cl, F or N;
  • L' is represented by formula (X) and wherein Z is selected from O, N, or CR 1 , wherein if Z is selected from O then n is selected from 0, and s is selected from 0.
  • L' is represented by formula (XI) wherein Z is selected from N or CR 1 .
  • the monoanion or the monoanionic ligand L' is selected from (V), (VI) or (VII)
  • the monoanion or the monoanionic ligand L' is selected from (V), or (VI)
  • the monoanion or the monoanionic ligand L' is selected from (V) wherein two adjacent substituents R a , R b , and R 1 can optionally be connected to form heterocycle or carbocycle.
  • the monoanionic ligand L' is selected from (V)
  • R a and R b are independently selected from perfluorinated C1 to C6 alkyl, CF3, substituted or unsubstituted C6 to C40 aryl, 3,5-CFi-phenyl, N, NR 5 , substituted or unsubstituted C2 to C40 heteroaryl, 2,6-CF3-pyridinyl, substituted or unsubstituted amine group having 0 to 20 carbon atoms; wherein the one or more substituents on R 1 are independently selected from D, electron-withdrawing group, halogen, F, CN, NO2, SF5, isonitrile, ester group, carboxylic group, carbonyl group, acyl group, thio group sulfinyl group, sulfonyl group, phosphine group, partially perfluorinated C1 to C12 alkyl, perfluorinated C1 to C12 alkyl, CF3, partially perfluorinated C1 to C6 alkoxy, per
  • the monoanionic ligand L' is selected from (V)
  • At least one of R a , R b , R c or R d or R a , R b , R c and R d is/are independently selected from DI to DI 05
  • R a , R b , R c or R d or R a , R b , R c and R d is/are independently selected from DI to DI 05 or NR 5 , wherein R 5 is independently selected from DI to D105.
  • the monoanion or the monoanionic ligand is selected from LI to L405:
  • the monoanion or the monoanionic ligand is selected from LI to L315, L319 to L327, L331 to L405.
  • the monoanion or the monoanionic ligand is selected from LI to L315, and L331 to L405
  • the monoanion or the monoanionic ligand is selected from LI to L265, and L331 to L405.
  • the monoanion or the monoanionic ligand is selected from LI to L265.
  • the monoanion or the monoanionic ligand is selected from LI to L54.
  • the monoanion or the monoanionic ligand is selected from L55 to L265.
  • compound of formula (II) is selected from the following:
  • the compound of formula (II) is present in the hole injection layer in an amount of ⁇ 99.9 mol% based on the total number of molecules in the hole injection layer, preferably ⁇ 99 mol% , more preferably 9 ⁇ 5 mol% , more preferably ⁇ 90 mol% , more preferably ⁇ 80 mol% , more preferably 7 ⁇ 0 mol% , more preferably ⁇ 60 mol% , more preferably ⁇ 50 mol% , more preferably 4 ⁇ 0 mol% , more preferably 30 ⁇ mol% , more preferably ⁇ 20 mol% , more preferably ⁇ 10 mol%, more preferably 7 ⁇ mol%, more preferably ⁇ 6 mol%, more preferably ⁇ 5 mol%, more preferably 4 ⁇ mol%, and most preferably ⁇ 3.0..
  • the first hole transport matrix compound is present in the hole injection layer in an amount of ⁇ 0.1 mol% based on the total number of molecules in the hole injection layer, preferably ⁇ 1 mol%, more preferably ⁇ 5 mol%, more preferably ⁇ 10 mol%, more preferably ⁇ 20 mol%, more preferably ⁇ 30 mol%, more preferably ⁇ 40 mol%, more preferably ⁇ 50 mol%, more preferably ⁇ 60 mol%, more preferably ⁇ 70 mol%, more preferably ⁇ 80 mol%, more preferably ⁇ 90 mol%, more preferably ⁇ 93 mol%, more preferably ⁇ 94 mol%, more preferably ⁇ 95 mol%, more preferably ⁇ 96 wt%, and most preferably ⁇ 97.0 mol%.
  • the organic electroluminescent device further comprises a third emission layer.
  • no more than one charge generation layer is arranged, in particular no more than one charge generation layer comprising a p-type charge generation layer and an n- type charge generation layer.
  • the second emission layer and the third emission layer no more than one charge generation layer is arranged, in particular no more than one charge generation layer comprising a p-type charge generation layer and an n-type charge generation layer.
  • a third emission layer and a second charge generation layer wherein the second charge generation layer is arranged between the second emission layer and the third emission layer, wherein the second charge generation layer comprises a second p-type charge generation layer and a second n-type charge generation layer, wherein the second n-type charge generation layer is closer to the anode layer than the second p-type charge generation layer, wherein the second n-type charge generation layer comprises a metal dopant and a matrix compound, wherein the second p-type charge generation layer comprises a second hole transport matrix compound and a compound of formula (I).
  • the organic electroluminescent device further comprises a third emission layer and a fourth emission layer.
  • the organic electroluminescent device comprises comprises a third emission layer, a fourth emission layer, a second charge generation layer, and third charge generation layer, wherein the second charge generation layer is arranged between the second emission layer and the third emission layer, wherein the third charge generation layer is arranged between the third and the fourth emission layer, wherein the second charge generation layer comprises a second p-type charge generation layer and a second n-type charge generation layer, wherein the third charge generation layer comprises a third p-type charge generation layer and a third n-type charge generation layer, wherein the second n-type charge generation layer is closer to the anode layer than the second p-type charge generation layer, wherein the third n-type charge generation layer is closer to the anode layer than the third p-type charge generation layer, wherein the second n-type charge generation layer comprises a metal dopant and a matrix compound, wherein the third n-type charge generation layer comprises a metal dopant and a matrix compound, wherein the second n-type charge generation layer comprises
  • the organic electroluminescent device further comprises a layer selected from hole injection layer, hole transport layer, electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, first electron blocking layer, second electron blocking layer, optionally a first hole blocking layer, optionally a second hole blocking layer, a first electron transport layer, a second electron transport layer, and an electron injection layer.
  • the first n-type charge generation layer is in direct contact to the first p-type charge generation layer.
  • the second n-type charge generation layer is in direct contact to the second p-type charge generation layer.
  • the third n-type charge generation layer is in direct contact to the third p-type charge generation layer.
  • each of the at least two light- emitting units comprises an electron transport layer.
  • the organic electroluminescent device further comprises an electron transport layer, wherein the electron transport layer is arranged between the first emission layer and the second emission layer, wherein the electron transport layer is arranged in direct contact to the first n-type charge generation layer, and wherein the electron transport layer is arranged between the first emission layer and the first n- type charge generation layer.
  • the organic electroluminescent device further comprises an electron transport layer, wherein the electron transport layer is arranged between the first emission layer and the second emission layer, wherein the electron transport layer is arranged in direct contact to the first n-type charge generation layer, and wherein the electron transport layer is arranged between the first emission layer and the first n- type charge generation layer, and wherein the first n-type charge generation layer is in direct contact to the to the first p-type charge generation layer.
  • the matrix compound of the first n-type charge generation layer is an electron transport material.
  • the matrix compound of the first n-type charge generation layer an organic electron transport material.
  • the at least one C2 to C24 N- heteroaryl may be selected from a compound comprising at least one azine group, preferably at least two azine groups, also preferred three azine groups.
  • the matrix compound of the first n- type charge generation layer comprises at least one group selected from the list consisting of pyridine, pyrimidine, triazine, imidazole, benzimidazole, benzooxazole, quinone, benzoquinone, imidazo[l,5-a]pyridine, quinoxaline, benzoquinoxaline, acridine, phenanthroline, benzoacridine, dibenzoacridine phosphine oxide, terpyridine.
  • the matrix compound of the first n- type charge generation layer comprises at least one phenanthroline group, preferably two phenanthroline groups, one or more pyridine groups, one or more pyrimidine groups, one or more triazine groups, one or more imidazo[l,5-a]pyridine groups, or one or more phosphine oxide groups.
  • the matrix compound of the first n- type charge generation layer comprises at least one phenanthroline group, preferably two phenanthroline groups, one or more pyridine groups, one or more pyrimidine groups, or one or more phosphine oxide groups.
  • the matrix compound of the first n- type charge generation layer comprises at least one phenanthroline group, preferably two phenanthroline groups, a pyridine group, a pyrimidine groups, or a phosphine oxide group.
  • the matrix compound of the first n- type charge generation layer comprises at least one phenanthroline group, preferably two phenanthroline groups, one or more pyridine groups, one or more pyrimidine groups, one or more triazine groups.
  • the matrix compound of the first n- type charge generation layer is selected from the group comprising 2,2'-(l,3-Phenylene)bis[9- phenyl-l,10-phenanthroline], (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracen-9- yl)phenyl)dimethylphosphine oxide, 3-(3-(9,10-diphenylanthracen-2-yl)phenyl)-l-(pyridin-2- yl)imidazo [ 1 , 5 -a] pyridine, 7-(3 -( 1 , 10-phenanthrolin-2-yl)phenyl)dibenzo [c,h]acridine, 7-(3 - ([2,2':6',2"-terpyridin]-4'-yl)phenyl)dibenzo[c,h]acridine, 4'-
  • the matrix compound of the first n- type charge generation layer comprises at least one phenanthroline group, preferably two phenanthroline groups.
  • the metal dopant is selected from a metal with an electronegativity of ⁇ 1.4 eV by Pauling scale or a metal alloy comprising a metal with an electronegativity of ⁇ 1.4 eV by Pauling scale.
  • the metal dopant is selected from a metal with an electronegativity of ⁇ 1.35 eV by Pauling scale or a metal alloy comprising a metal with an electronegativity of ⁇ 1.35 eV by Pauling scale.
  • the metal dopant is a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb or a metal alloy comprising a metal selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Sm, Eu and Yb.
  • the metal dopant is a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb or a metal alloy comprising a metal selected from the group consisting of Li, Na, K, Cs, Mg, Ca, Ba, Sm, Eu and Yb.
  • the metal dopant is a metal selected from the group consisting of Li, Mg and Yb or a metal alloy comprising a metal selected from the group consisting of Li, Mg and Yb.
  • the metal dopant is a metal selected from the group consisting of Li and Yb or a metal alloy comprising a metal selected from the group consisting of Li, and Yb.
  • the metal dopant is Yb or a metal alloy comprising a metal selected from the group consisting of Li and Yb.
  • the metal dopant is Yb.
  • the metal dopant is in the oxidations state ⁇ 0.
  • the metal dopant is present in the first n-type charge generation layer in an amount of ⁇ 99.9 vol% based on the total volume of the layer, preferably ⁇ 99 vol%, more preferably ⁇ 95 vol%, more preferably 9 ⁇ 0 vol%, more preferably ⁇ 80 vol%, more preferably ⁇ 70 vol%, more preferably 6 ⁇ 0 vol% , more preferably ⁇ 50 vol%, more preferably ⁇ 40 vol%, more preferably 3 ⁇ 0 vol%, more preferably 2 ⁇ 0 vol%, more preferably ⁇ 10 vol%, more preferably ⁇ 5 vol% , more preferably 3 ⁇ .0 vol%, more preferably ⁇ 2 vol%, more preferably ⁇ 1.5 vol%, more preferably ⁇ 1.25 vol%, and most preferably ⁇ 1.0 vol%.
  • the matrix compound is present in the first n-type charge generation layer in an amount of ⁇ 0.1 vol% based on the total volume of the layer, preferably ⁇ 1 vol%, more preferably ⁇ 5 vol%, more preferably ⁇ 10 vol%, more preferably ⁇ 20 vol%, more preferably ⁇ 30 vol%, more preferably ⁇ 40 vol%, more preferably ⁇ 50 vol%, more preferably ⁇ 60 vol%, more preferably ⁇ 70 vol%, more preferably ⁇ 80 vol%, more preferably ⁇ 90 vol%, more preferably ⁇ 95 vol%, more preferably ⁇ 97.0 vol%, more preferably ⁇ 98 vol%, more preferably ⁇ 98.25 vol%, more preferably ⁇ 98.5 vol%, more preferably ⁇ 98.75 vol% and most preferably ⁇ 99.0 vol%.
  • the compound of formula (I) is present in the first p-type charge generation layer in an amount of ⁇ 99.9 mol% based on the total numbers of molecules in the p-type charge generation layer, preferably 99 ⁇ mol%, more preferably ⁇ 95 mol%, more preferably ⁇ 90 mol%, more preferably ⁇ 80 mol%, more preferably ⁇ 70 mol%, more preferably ⁇ 60 mol%, more preferably ⁇ 50 mol%, more preferably ⁇ 40 mol%, more preferably ⁇ 30 mol%, more preferably ⁇ 20 mol%, more preferably ⁇ 10 mol%, and more preferably ⁇ 7 mol%,
  • the second hole transport matrix compound is present in the first p-type charge generation layer in an amount of ⁇ 0.1 mol% based on the total number of molecules in the p-type charge generation layer, preferably ⁇ 1 mol%, more preferably ⁇ 5 mol%, more preferably ⁇ 10 mol%, more preferably ⁇ 20 mol%, more preferably ⁇ 30 mol%, more preferably ⁇ 40 mol%, more preferably ⁇ 50 mol%, more preferably ⁇ 60 mol%, more preferably ⁇ 70 mol%, more preferably ⁇ 80 mol%, more preferably ⁇ 90 mol%, and more preferably ⁇ 93 mol%.
  • the electroluminescent device further comprises at least one hole transport layer.
  • the organic electroluminescent device further comprises a hole transport layer, wherein the hole transport layer is arranged between the first emission layer and the second emission layer, wherein the hole transport layer is arranged in direct contact to the first p-type charge generation layer, and wherein the hole transport layer is arranged between the first p-type charge generation layer and the second emission layer.
  • the organic electroluminescent device further comprises a hole transport layer, wherein the hole transport layer is arranged between the first emission layer and the second emission layer, wherein the hole transport layer is arranged in direct contact to the first p-type charge generation layer, and wherein the hole transport layer is arranged between the first p-type charge generation layer and the second emission layer, and wherein the first n-type charge generation layer is arranged in direct contact to the hole transport layer.
  • the first hole transport matrix compound has a calculated HOMO energy level, expressed in the absolute scale referring to vacuum energy level being zero, in the range of ⁇ -4.27 eV to ⁇ -5.1 eV, when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31 G* basis set in the gas phase, preferably ⁇ -4.3 eV to ⁇ -5.0 eV, more preferably - ⁇ 4.4 eV and ⁇ -5.0 eV, more preferably ⁇ -4.5 eV and ⁇ -5.0 eV, more preferably ⁇ -4.5 eV and ⁇ -4.9 eV and most preferably ⁇ -4.6 eV and ⁇ -4.9 eV.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the first hole transport matrix compound is a substantially covalent matrix compound.
  • the first hole transport matrix compound is an organic hole transport matrix compound.
  • the first hole transport matrix compound is a substantially covalent organic matrix compound.
  • the first hole transport matrix compound of the p-type charge generation layer is a substantially covalent matrix compound.
  • the organic hole transport matrix compound of the charge generation layer is the same as the organic hole transport matrix compound of the p-type charge generation layer.
  • the second hole transport matrix compound of the p-type charge generation layer is the same as the first hole transport matrix compound of the hole injection layer.
  • the first hole transport matrix compound of the hole injection layer has a calculated HOMO energy level, expressed in the absolute scale referring to vacuum energy level being zero, in the range of - ⁇ 4.27 eV to ⁇ -5.1 eV, when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase, preferably ⁇ -4.3 eV to ⁇ -5.0 eV, more preferably ⁇ -4.4 eV and ⁇ -5.0 eV, more preferably ⁇ -4.5 eV and ⁇ -5.0 eV, more preferably ⁇ -4.5 eV and ⁇ -4.9 eV and most preferably ⁇ -4.6 eV and ⁇ -4.9 eV.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the first hole transport matrix compound is a substantially covalent matrix compound.
  • the first hole transport matrix compound is an organic hole transport matrix compound.
  • the first hole transport matrix compound is a substantially covalent organic matrix compound.
  • the first hole transport matrix compound is present in the hole injection layer in an amount of ⁇ 0.1 mol% based on the total number of molecules in the hole injection layer, preferably ⁇ 1 mol%, more preferably ⁇ 5 mol%, more preferably ⁇ 10 mol%, more preferably ⁇ 20 mol%, more preferably ⁇ 30 mol%, more preferably ⁇ 40 mol%, more preferably ⁇ 50 mol%, more preferably ⁇ 60 mol%, more preferably ⁇ 70 mol%, more preferably ⁇ 80 mol%, more preferably ⁇ 90 mol%, more preferably ⁇ 93 mol%, more preferably ⁇ 94 mol%, more preferably ⁇ 95 mol%, more preferably ⁇ 96 wt%, and most preferably ⁇ 97.0 mol%.
  • the organic hole transport matrix compound of the p-type charge generation layer is the same as the organic hole transport layer of the hole injection layer.
  • the second hole transport matrix compound of the p-type charge generation layer has a calculated HOMO energy level, expressed in the absolute scale referring to vacuum energy level being zero, in the range of ⁇ -4.27 eV to ⁇ - 5.1 eV, when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase, preferably ⁇ -4.3 eV to ⁇ -5.0 eV, more preferably ⁇ -4.4 eV to ⁇ -5.0 eV, more preferably ⁇ -4.5 eV and ⁇ -5.0 eV, more preferably ⁇ -4.5 eV and ⁇ -4.9 eV and most preferably ⁇ -4.6 eV and ⁇ -4.9 eV.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135
  • the second hole transport matrix compound is a substantially covalent matrix compound.
  • the second hole transport matrix compound is an organic hole transport matrix compound.
  • the second hole transport matrix compound is a substantially covalent organic matrix compound.
  • the second hole transport matrix compound is present in the p-type charge generation layer in an amount of ⁇ 0.1 mol% based on the total number of molecules in the p-type charge generation layer, preferably ⁇ 1 mol%, more preferably ⁇ 5 mol%, more preferably ⁇ 10 mol%, more preferably ⁇ 20 mol%, more preferably ⁇ 30 mol%, more preferably ⁇ 40 mol%, more preferably ⁇ 50 mol%, more preferably ⁇ 60 mol%, more preferably ⁇ 70 mol%, more preferably ⁇ 80 mol%, more preferably ⁇ 90 mol%, and more preferably ⁇ 93 mol%.
  • the organic electroluminescent device comprises at least one electron injection layer (EIL).
  • EIL electron injection layer
  • the electron injection layer is in direct contact to the cathode layer.
  • the organic hole transport matrix compound of the p-type charge generation layer is a substantially covalent matrix compound and the same as the organic hole transport matrix compound of the hole injection layer.
  • the substantially covalent matrix compound may be selected from at least one organic compound.
  • the substantially covalent matrix may consists substantially from covalently bound C, H, O, N, S, which optionally comprise in addition covalently bound B, P, As and/or Se.
  • the substantially covalent matrix compound may be selected from organic compounds consisting substantially from covalently bound C, H, O, N, S, which optionally comprise in addition covalently bound B, P, As and/or Se.
  • Organometallic compounds comprising covalent bonds carbon-metal, metal complexes comprising organic ligands and metal salts of organic acids are further examples of organic compounds that may serve as substantially covalent matrix compounds of the hole injection layer.
  • the substantially covalent matrix compound lacks metal atoms and majority of its skeletal atoms may be selected from C, O, S, N.
  • the substantially covalent matrix compound lacks metal atoms and majority of its skeletal atoms may be selected from C and N.
  • the substantially covalent matrix compound may have a molecular weight Mw of ⁇ 400 and ⁇ 2000 g/mol, preferably a molecular weight Mw of ⁇ 450 and ⁇ 1500 g/mol, further preferred a molecular weight Mw of ⁇ 500 and ⁇ 1000 g/mol, in addition preferred a molecular weight Mw of ⁇ 550 and ⁇ 900 g/mol, also preferred a molecular weight Mw of ⁇ 600 and ⁇ 800 g/mol.
  • the substantially covalent matrix compound comprises at least one arylamine moiety, alternatively a diarylamine moiety, alternatively a triarylamine moiety.
  • the substantially covalent matrix compound is free of metals and/or ionic bonds.
  • the substantially covalent matrix compound may comprises at least one arylamine compound, diarylamine compound, triarylamine compound, a compound of formula (XII) or a compound of formula (XIII): wherein:
  • T 1 , T 2 , T 3 , T 4 and T 5 are independently selected from a single bond, phenylene, biphenylene, terphenylene or naphthenylene, preferably a single bond or phenylene;
  • T 6 is phenylene, biphenylene, terphenylene or naphthenylene
  • Ar’ 1 , Ar’ 2 , Ar’ 3 , Ar’ 4 and Ar’ 5 are independently selected from substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C3 to C20 heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9- fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted tetracene, substituted or unsubstituted tetraphene, substituted or unsubstituted dibenzofurane, substituted or unsubstituted
  • T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a single bond, phenylene, biphenylene or terphenylene. According to an embodiment wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from phenylene, biphenylene or terphenylene and one of T 1 , T 2 , T 3 , T 4 and T 5 are a single bond. According to an embodiment wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from phenylene or biphenylene and one of T 1 , T 2 , T 3 , T 4 and T 5 are a single bond. According to an embodiment wherein T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from phenylene or biphenylene and two of T 1 , T 2 , T 3 , T 4 and T 5 are a single bond.
  • T 1 , T 2 and T 3 may be independently selected from phenylene and one of T 1 , T 2 and T 3 are a single bond. According to an embodiment wherein T 1 , T 2 and T 3 may be independently selected from phenylene and two of T 1 , T 2 and T 3 are a single bond.
  • T 6 may be phenylene, biphenylene, terphenylene. According to an embodiment wherein T 6 may be phenylene. According to an embodiment wherein T 6 may be biphenylene. According to an embodiment wherein T 6 may be terphenylene.
  • Ar’ 1 , Ar’ 2 , Ar’ 3 , Ar’ 4 and Ar’ 5 may be independently selected from El to El 6:
  • Ar’ 1 , Ar’ 2 , Ar’ 3 , Ar’ 4 and Ar’ 5 may be independently selected from El to El 5; alternatively selected from El to E10 and El 3 to El 5.
  • Ar’ 1 , Ar’ 2 , Ar’ 3 , Ar’ 4 and Ar’ 5 may be independently selected from the group consisting of El, E2, E5, E7, E9, E10, El 3 to El 6.
  • the rate onset temperature may be in a range particularly suited to mass production, when Ar’ 1 , Ar’ 2 , Ar’ 3 , Ar’ 4 and Ar’ 5 are selected in this range.
  • the “matrix compound of formula (XII) or formula (XIII)“ may be also referred to as “hole transport compound”.
  • the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and/or substituted fluorenyl group, wherein the substituents are independently selected from methyl, phenyl or fluorenyl.
  • matrix compound of formula (XII) or formula (XIII) are selected from Fl to F20:
  • the electronic organic device is an organic light emitting diode.
  • the electroluminescent device is an organic light emitting diode, wherein light is emitted through the cathode layer.
  • the present invention furthermore relates to a display device comprising an organic electroluminescent device according to the present invention.
  • the display device comprising an organic electroluminescent device according to the present invention, wherein the cathode layer is transparent.
  • p-type charge generation layer
  • the p-type charge generation layer may be formed on the anode layer or cathode layer by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like.
  • the deposition conditions may vary according to the compound(s) that are used to form the layer, and the desired structure and thermal properties of the layer. In general, however, conditions for vacuum deposition may include a deposition temperature of 100° C to 350° C, a pressure of 10' 8 to 10' 3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm/sec.
  • coating conditions may vary according to the compound(s) that are used to form the layer, and the desired structure and thermal properties of the organic semiconductor layer.
  • the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 80° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.
  • the thickness of the p-type charge generation layer may be in the range from about 1 nm to about 20 nm, and for example, from about 2 nm to about 15 nm, alternatively about 2 nm to about 12 nm.
  • a hole injection layer may be formed on the anode layer by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like.
  • the deposition conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. In general, however, conditions for vacuum deposition may include a deposition temperature of 100° C to 500° C, a pressure of 10' 8 to 10' 3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm/sec.
  • coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL.
  • the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 80° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.
  • the thickness of the HIL may be in the range from about 1 nm to about 100 nm, and for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injecting characteristics, without a substantial penalty in driving voltage.
  • the organic electroluminescent device may comprise, besides the layers already mentioned above, further layers. Exemplary embodiments of respective layers are described in the following:
  • the substrate may be any substrate that is commonly used in manufacturing of, electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate shall be a transparent or semitransparent material, for example a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate may be both a transparent as well as a non-transparent material, for example a glass substrate, a plastic substrate, a metal substrate, a silicon substrate or a backplane.
  • the anode layer may be formed by depositing or sputtering a material that is used to form the anode layer.
  • the material used to form the anode layer may be a high work-function material, so as to facilitate hole injection.
  • the anode material may also be selected from a low work function material (i.e. aluminum).
  • the anode electrode may be a transparent or reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin-dioxide (SnO2), aluminum zinc oxide (A1Z0) and zinc oxide (ZnO), may be used to form the anode electrode.
  • the anode layer may also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.
  • the organic electronic device according to the present invention may further comprise at least one hole transport layer (HTL).
  • HTL hole transport layer
  • the at least one hole transport layer is comprised in one of the at least two light-emitting units, wherein preferably at least one hole transport layer is comprised in each light-emitting unit.
  • a hole transport layer may be formed on the HIL or CGL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL or CGL.
  • the conditions for the vacuum or solution deposition may vary, according to the compound that is used to form the HTL.
  • the HTL may be formed of any compound that is commonly used to form a HTL.
  • Compounds that can be suitably used are disclosed for example in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 and incorporated by reference.
  • Examples of the compound that may be used to form the HTL are: carbazole derivatives, such as N- phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[l,l-biphenyl]-4,4'-diamine (TPD), or N,N'-di(naphthalen-l-yl)-N,N'-diphenyl benzidine (a-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N- carbazolyl)triphenylamine (TCTA).
  • TCTA can transport holes and inhibit excitons from being diffused into the EML.
  • the hole transport layer may comprise a substantially covalent matrix compound as described above.
  • the hole injection layer and the hole transport layer may comprise an identical substantially covalent matrix compound as described above.
  • the hole transport layer may comprise a compound of formula (XII) or (XIII) as described above.
  • the hole injection layer and the hole transport layer may comprise an identical compound of formula (XII) or (XIII) as described above.
  • the p-type charge generation layer, the hole injection layer and the hole transport layer may comprise an identical substantially covalent matrix compound.
  • the p-type charge generation layer, the hole injection layer and the hole transport layer may comprise an identical an identical compound of formula (XII) or (XIII) as described above.
  • the thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably, about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm.
  • a preferred thickness of the HTL may be 170 nm to 200 nm.
  • the HTL may have excellent hole transporting characteristics, without a substantial penalty in driving voltage.
  • an electron blocking layer is to prevent electrons from being transferred from an emission layer to the hole transport layer and thereby confine electrons to the emission layer. Thereby, efficiency, operating voltage and/or lifetime are improved.
  • the electron blocking layer comprises a triarylamine compound.
  • the triarylamine compound may have a LUMO level closer to vacuum level than the LUMO level of the hole transport layer.
  • the electron blocking layer may have a HOMO level that is further away from vacuum level compared to the HOMO level of the hole transport layer.
  • the thickness of the electron blocking layer may be selected between 2 and 20 nm.
  • the electron blocking layer has a high triplet level, it may also be described as triplet control layer.
  • the function of the triplet control layer is to reduce quenching of triplets if a phosphorescent green or blue emission layer is used. Thereby, higher efficiency of light emission from a phosphorescent emission layer can be achieved.
  • the triplet control layer is selected from triarylamine compounds with a triplet level above the triplet level of the phosphorescent emitter in the adjacent emission layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2 722 908 Al.
  • the organic electronic device may further comprise a photoactive layer, wherein the photoactive layer is arranged between the anode layer and the cathode layer.
  • the photoactive layer converts an electrical current into photons or photons into an electrical current.
  • the PAL may be formed on the HTL by vacuum deposition, spin coating, slot-die coat- ing, printing, casting, LB deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the PAL.
  • the photoactive layer may be a light-emitting layer or a light-absorbing layer, in particular a light-emitting layer.
  • Emission layer Emission layer
  • the organic electronic device may further comprise an emission layer, wherein the emission layer is arranged between the anode layer and the cathode layer.
  • the EML may be formed on the HTL by vacuum deposition, spin coating, slot-die coat- ing, printing, casting, LB deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the EML.
  • the emission layer may be formed of a combination of a host and an emitter dopant.
  • Example of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n- vinylcarbazole) (PVK), 9, 10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)- triphenylamine(TCTA), l,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl- 9,10-di-2-naphthylanthracenee (TBADN), distyrylarylene (DS A) and bis(2-(2- hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2).
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • PVK poly(n-
  • the emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters which emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency.
  • the emitter may be a small molecule or a polymer.
  • red emitter dopants examples include PtOEP, Ir(piq)3, and Btp21r(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants could also be used.
  • Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and ter-fluorene.
  • phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and ter-fluorene.
  • 4.4'-bis(4-diphenyl amiostyryl)biphenyl (DPAVBi), 2,5,8,11-tetra- tert-butyl perylene (TBPe) are examples of fluorescent blue emitter dopants.
  • the amount of the emitter dopant may be in the range from about 0.01 to about 50 parts by weight, based on 100 parts by weight of the host.
  • the emission layer may consist of a light-emitting polymer.
  • the EML may have a thickness of about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission, without a substantial penalty in driving voltage.
  • HBL Hole blocking layer
  • a hole blocking layer may be formed on the EML, by using vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like, in order to prevent the diffusion of holes into the ETL.
  • the HBL may have also a triplet exciton blocking function.
  • the HBL may also be named auxiliary ETL or a-ETL.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the HBL. Any compound that is commonly used to form a HBL may be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives and azine derivatives, preferably triazine or pyrimidine derivatives.
  • the HBL may have a thickness in the range from about 5 nm to about 100 nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties, without a substantial penalty in driving voltage.
  • Electron transport layer ETL
  • the organic electronic device according to the present invention may further comprise at least one electron transport layer (ETL).
  • ETL electron transport layer
  • the at least one electron transport layer is comprised in one of the at least two light-emitting units, wherein preferably at least one electron transport layer is comprised in each light-emitting unit.
  • the electron transport layer may further comprise an azine compound, preferably a pyridine, pyrimidine or triazine compound, and most preferably a triazine compound or a pyrimidine compound.
  • an azine compound preferably a pyridine, pyrimidine or triazine compound, and most preferably a triazine compound or a pyrimidine compound.
  • the electron transport layer may further comprise 2-([l,l'-biphenyl]-4-yl)-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-l,3,5- triazine, 2-(3-(2, 6-dimethylpyridin-3-yl)-5-(phenanthren-9-yl)phenyl)-4,6-diphenyl- 1,3,5- triazine, 3'-(4-phenyl-6-(spiro[fluorene-9,9'-xanthen]-2'-yl)-l,3,5-triazin-2-yl)-[l,l'-biphenyl]-4- carbonitrile, and 4'-(4-(4-(4,6-diphenyl-l,3,5-triazin-2-yl)phenyl)naphthalen-l-yl)-[l,l'- biphenyl]-4-carbonitrile, and 4'-(4-
  • the electron transport layer may further comprise a dopant selected from an alkali organic complex, preferably LiQ.
  • the thickness of the ETL may be in the range from about 15 nm to about 50 nm, for example, in the range from about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL may have satisfactory electron-injecting properties, without a substantial penalty in driving voltage.
  • the organic electronic device may further comprise a hole blocking layer and an electron transport layer, wherein the hole blocking layer and the electron transport layer comprise an azine compound.
  • the azine compound is a pyridine, pyrimidine or triazine compound, and most preferably a triazine compound.
  • Electron injection layer An optional EIL, which may facilitates injection of electrons from the cathode, may be formed on the ETL preferably closest to the cathode, and more preferably directly on the electron transport layer.
  • materials for forming the EIL include lithium 8- hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg which are known in the art.
  • Deposition and coating conditions for forming the EIL are similar to those for formation of the HIL, although the deposition and coating conditions may vary, according to the material that is used to form the EIL.
  • the thickness of the EIL may be in the range from about 0.1 nm to about 10 nm, for example, in the range from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron- injecting properties, without a substantial penalty in driving voltage.
  • the cathode layer is formed on the ETL or optional EIL.
  • the cathode layer may be formed of a metal, an alloy, an electrically conductive compound, or a mixture thereof.
  • the cathode electrode may have a low work function.
  • the cathode layer may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like.
  • the cathode electrode may be formed of a transparent conductive oxide, such as ITO or IZO.
  • the thickness of the cathode layer may be in the range from about 5 nm to about 1000 nm, for example, in the range from about 10 nm to about 100 nm.
  • the cathode layer may be transparent or semitransparent even if formed from a metal or metal alloy.
  • the cathode layer comprises a metal or metal alloy and is transparent.
  • the cathode layer is not part of an electron injection layer or the electron transport layer.
  • the organic electroluminescent device comprises, preferably in the following order, an anode layer; a hole injection layer; a first hole transport layer; a first electron blocking layer ; a first emission layer; a first optional hole blocking layer; and a first electron transport layer; wherein the hole injection layer is in direct contact to the anode layer, and wherein the hole injection layer comprises a first hole transport matrix compound and a compound of formula (II) which is a metal compound selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms; a first charge generation layer disposed over the first electron transport layer, wherein the first charge generation layer comprises a first n-type charge generation layer, and a first p-type charge generation layer, wherein the first p-type charge generation layer, comprise
  • the organic electroluminescent device comprises, preferably in the following order, an anode layer, a hole injection layer , a hole transport layer, a first electron blocking layer, and a first emission layer
  • the hole injection layer comprises a first hole transport matrix compound and a compound of formula (II) which is a metal compound selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms
  • the hole injection layer is in direct contact to the anode layer, a first optional hole blocking layer, a first electron transport layer, a first charge generation layer disposed over the first electron transport layer , wherein the first charge generation layer comprises a first n-type charge generation layer , and a first p-type charge generation layer , wherein the first p-type charge generation layer comprise a second hole transport matrix compound, and
  • the organic electroluminescent device comprises, preferably in the following order, an anode layer , a hole injection layer , a hole transport layer , a first electron blocking layer , a first emission layer ; wherein the hole injection layer comprises a first hole transport matrix compound and a compound of formula (II) which is a metal compound selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms, and wherein the hole injection layer is in direct contact to the anode layer; a first optional hole blocking layer ; a first electron transport layer ; a first charge generation layer disposed over the first electron transport layer , wherein the first charge generation layer comprises a first n-type charge generation layer , and a first p-type charge generation layer , wherein the first p-type charge generation layer comprise a second hole transport
  • FIG. 1 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 2 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 3 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 4 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures.
  • first element when a first element is referred to as being formed or disposed “on” or “onto” a second element, the first element can be disposed directly on the second element, or one or more other elements may be disposed there between.
  • first element when referred to as being formed or disposed "directly on” or “directly onto” a second element, no other elements are disposed there between.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a first emission layer (EML1) 145, wherein the hole injection layer (HIL) 130 comprises a hole transport matrix compound and a metal compound, wherein the metal compound is selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms.
  • ANO anode layer
  • HIL hole injection layer
  • EML1 first emission layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGL1) 160, wherein the first charge generation layer (CGL1) 160 comprises a first n-type charge generation layer (n-CGLl) 161, and a first p-type charge generation layer (p-CGLl) 162, wherein the first n-type charge generation layer (n-CGLl) 161 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the organic electroluminescent device 100 further comprises a second emission layer (EML2) 245, and a cathode layer (CAT) 190.
  • EML2 second emission layer
  • CAT cathode layer
  • Fig. 2 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EML1) 145, a first optional hole blocking layer (HBL1) 147, and a first electron transport layer (ETL1) 149, wherein the hole injection layer (HIL) 130 comprises a first hole transport matrix compound and a compound of formula (II) which is a metal compound selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms.
  • the organic electroluminescent device further comprises a first charge generation layer (CGL1) 160 disposed over the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 comprises a first n-type charge generation layer (n-CGLl) 161, and a first p-type charge generation layer (p-CGLl) 162, wherein the first p-type charge generation layer (p-CGLl) 162 comprise a second hole transport matrix compound, and a compound of formula (I); wherein the first n-type charge generation layer (n-CGLl) 161 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242.
  • HTL2 second hole transport layer
  • EBL2 second electron blocking layer
  • the organic electroluminescent device 100 further comprises a second emission layer (EML2) 245.
  • EML2 second emission layer
  • the organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
  • HBL2 hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • CAT cathode layer
  • Eig. 3 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, and a first emission layer (EML1) 145; wherein the hole injection layer (HIL) 130 comprises a first hole transport matrix compound and a compound of formula (II) which is a metal compound selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms.
  • ANO anode layer
  • HIL hole injection layer
  • HTL1 hole transport layer
  • EBL1 electron blocking layer
  • EML1 first emission layer
  • the organic electroluminescent device 100 further comprises a first optional hole blocking layer (HBL1) 147.
  • HBL1 hole blocking layer
  • the organic electroluminescent device 100 further comprises a first electron transport layer (ETL 1) 149.
  • ETL 1 first electron transport layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGL1) 160 disposed over the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 comprises a first n-type charge generation layer (n-CGLl) 161, and a first p-type charge generation layer (p-CGLl) 162, wherein the first p-type charge generation layer (p-CGLl) 162 comprise a second hole transport matrix compound, and a compound of formula (I); wherein the first n-type charge generation layer (n-CGLl) 161 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, and a second electron blocking layer (EBL2) 242.
  • HTL2 second hole transport layer
  • EBL2 second electron blocking layer
  • the organic electroluminescent device 100 further comprises a second emission layer (EML2) 245.
  • EML2 second emission layer
  • the organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247.
  • HBL2 hole blocking layer
  • the organic electroluminescent device 100 further comprises a second electron transport layer (ETL2) 249.
  • ETL2 second electron transport layer
  • the organic electroluminescent device further comprises a second charge generation layer (CGL2) 260 disposed over the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 comprises a second n-type charge generation layer (n- CGL2) 261, and a second p-type charge generation layer (p-CGL2) 262, wherein the second p- type charge generation layer (p-CGL2) 262 comprise a second hole transport matrix compound, and a compound of formula (I); wherein the second n-type charge generation layer (n-CGL2) 261 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium, Magnesium.
  • the organic electroluminescent device 100 further comprises a third hole transport layer (HTL3) 341, and a third electron blocking layer (EBL3) 342.
  • HTL3 hole transport layer
  • EBL3 third electron blocking layer
  • the organic electroluminescent device 100 further comprises a third emission layer (EML3) 345.
  • EML3 third emission layer
  • the organic electroluminescent device 100 further comprises a third optional hole blocking layer (HBL3) 347, an electron transport layer (ETL)148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
  • HBL3 hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • CAT cathode layer
  • Fig. 4 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EML1) 145; wherein the hole injection layer (HIL) 130 comprises a first hole transport matrix compound and a compound of formula (II) which is a metal compound selected from a metal salt or metal complex comprising a metal cation and at least one monoanion consisting of at least 20 covalently bound atoms and/or at least one monoanionic ligand consisting of at least 20 covalently bound atoms.
  • ANO anode layer
  • HIL hole injection layer
  • HTL1 hole transport layer
  • EBL1 electron blocking layer
  • EML1 first emission layer
  • the organic electroluminescent device 100 further comprises a first optional hole blocking layer (HBL1) 147.
  • HBL1 hole blocking layer
  • the organic electroluminescent device 100 further comprises a first electron transport layer (ETL1) 149.
  • ETL1 first electron transport layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGL1) 160 disposed over the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 comprises a first n-type charge generation layer (n-CGLl) 161, and a first p-type charge generation layer (p-CGLl) 162, wherein the first p-type charge generation layer (p-CGLl) 162 comprise a second hole transport matrix compound, and a compound of formula (I); wherein the first n-type charge generation layer (n-CGLl) 161 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the metal dopant is selected from Ytterbium, Lithium or Magnesium.
  • the organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, and a second electron blocking layer (EBL2) 242.
  • HTL2 second hole transport layer
  • EBL2 second electron blocking layer
  • the organic electroluminescent device 100 further comprises a second emission layer (EML2) 245.
  • EML2 second emission layer
  • the organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247.
  • HBL2 hole blocking layer
  • the organic electroluminescent device 100 further comprises a second electron transport layer (ETL2) 249.
  • ETL2 second electron transport layer
  • the organic electroluminescent device further comprises a second charge generation layer (CGL2) 260 disposed over the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 comprises a second n-type charge generation layer (n- CGL2) 261, and a second p-type charge generation layer (p-CGL2) 262, wherein the second p- type charge generation layer (p-CGL2) 262 comprise a second hole transport matrix compound, and a compound of formula (I), wherein the second n-type charge generation layer (n-CGL2) 261 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium, Magnesium; .
  • the organic electroluminescent device 100 further comprises a third hole transport layer (HTL3) 341, and a third electron blocking layer (EBL3) 342.
  • HTL3 hole transport layer
  • EBL3 third electron blocking layer
  • the organic electroluminescent device 100 further comprises a third emission layer (EML3) 345.
  • EML3 third emission layer
  • the organic electroluminescent device 100 further comprises a third optional hole blocking layer (HBL3) 347.
  • HBL3 hole blocking layer
  • the organic electroluminescent device 100 further comprises a third electron transport layer (ETL3) 349,.
  • ETL3 third electron transport layer
  • the organic electroluminescent device further comprises a charge generation layer (CGL3) 360 disposed over the third electron transport layer (ETL3) 349, wherein the third charge generation layer (CGL3) 360 comprising a third n-type charge generation layer (n-CGL3) 361, and a third p-type charge generation layer (p-CGL3) 362, wherein the third p-type charge generation layer (p-CGL3) 362 comprise a second hole transport matrix compound, and a compound of formula (I); wherein the third n-type charge generation layer (n-CGL3) 361 comprises a matrix compound and a metal dopant, wherein preferably the metal dopant is selected from Ytterbium, Lithium or Magnesium, .
  • the organic electroluminescent device 100 further comprises a fourth hole transport layer (HTL4) 441, and a fourth electron blocking layer (EBL4) 442.
  • HTL4 hole transport layer
  • EBL4 fourth electron blocking layer
  • the organic electroluminescent device 100 further comprises a fourth emission layer (EML4) 345.
  • EML4 emission layer
  • the organic electroluminescent device 100 further comprises a fourth optional hole blocking layer (HBL4) 447, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
  • HBL4 hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • CAT cathode layer
  • the invention is furthermore illustrated by the following examples which are illustrative only and non-binding.
  • the HOMO of the hole transport matrix compound and the LUMO for compounds with formula (I) are calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany).
  • the optimized geometries and the HOMO and LUMO energy levels of the molecular structures are determined by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase.
  • the conformation with the lowest total energy is selected.
  • a glass substrate with an anode layer comprising a first anode sub-layer of 8 nm ITO, a second anode sub-layer of 120 nm Ag, and a third anode sub-layer of 10 nm ITO was cut to a size of 25 mm x 25 mm x 0.7 mm, ultrasonically washed with water for 60 minutes and then with isopropanol for 20 minutes.
  • the liquid film was removed in a nitrogen stream, followed by plasma treatment, to prepare the anode layer.
  • the plasma treatment was performed in nitrogen atmosphere or in an atmosphere comprising 98 vol.-% nitrogen and 2 vol.-% oxygen.
  • HIL hole injection layer
  • a first hole transport layer (HTL1) having a thickness of 27 nm is formed on the HIL by depositing F3 (N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine).
  • a first electron blocking layer (EBL1) having a thickness of 5 nm is formed on the HTL1 by depositing N-([l,l'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H- fluoren-2-amine.
  • a first emission layer (EML1) having a thickness of 20 nm is formed on the EBL1 by co-depositing 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant.
  • a first hole blocking layer having a thickness of 5 nm is formed on the first emission layer by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[l,l'-biphenyl]-3-yl)-4,6- dipheny 1- 1 , 3 , 5 -triazine.
  • a first electron transport layer (ETL1) having a thickness of 20 nm is formed on the first emission layer by co-depositing 4'-(4-(4-(4,6-diphenyl-l,3,5-triazin-2-yl)phenyl)naphthalen- l-yl)-[l,l'-biphenyl]-4-carbonitrile and LiQ in a ratio of 50:50 wt.-%.
  • the n-CGL having a thickness of 10 nm is formed on the ETL by co-depositing 99 vol.-% 2,2'-(l,3-Phenylene)bis[9-phenyl-l,10-phenanthroline] and 1 vol.-% Yb.
  • the p-CGL having a thickness of 10 nm is formed on the n-CGL by co-depositing F3 (N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2- amine) as a matrix compound and dopant compound.
  • F3 N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2- amine
  • a second hole transport layer (HTL2) having a thickness of 24 nm is formed on the p-CGL by depositing F3 (N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine).
  • F3 N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine.
  • EBL2 second electron blocking layer
  • a second emission layer having a thickness of 20 nm is formed on the EBL2 by co-depositing 97 vol.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 vol.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant.
  • HBL2 second hole blocking layer having a thickness of 5 nm is formed on the EML2 by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[l,l'-biphenyl]-3-yl)-4,6-diphenyl- 1,3,5-triazine.
  • a second electron transport layer having a thickness of 30 nm is formed on the HBL by co-depositing 4'-(4-(4-(4,6-diphenyl-l,3,5-triazin-2-yl)phenyl)naphthalen-l-yl)-[l,l'- biphenyl]-4-carbonitrile and LiQ in a ratio of 50:50 wt.-%.
  • an electron injection layer having a thickness of 2 nm is formed on the ETL2 by depositing Yb.
  • the cathode layer having a thickness of 13 nm is formed on the EIL by co-depositing Ag:Mg (90: 10 vol.-%) at a rate of 0.01 to 1 A/s at 10' 7 mbar.
  • a capping layer having a thickness of 75 nm is formed on the cathode layer by depositing compound F3 (N-([l,l'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine).
  • the OLED stack is protected from ambient conditions by encapsulation of the device with a glass slide. Thereby, a cavity is formed, which includes a getter material for further protection.
  • a substrate with dimensions of 150 mm x 150 mm x 0.7 mm was ultrasonically cleaned with 2% aqueous solution of Deconex FPD 211 for 7 minutes and then pure water for 5 minutes, and dried for 15 minutes in a spin dryer. Subsequently, Ag was deposited as anode at a pressure of 10' 5 to 10' 7 mbar on the substrate.
  • N-( ⁇ [l,l-‘biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)- 9H-fluoren-2-amine ⁇ was vacuum deposited on the HIL, to form a first HTL having a thickness of 128 nm.
  • N-([l,r-biphenyl]-4-yl)-9,9-diphenyl-N-(4-triphenylsilyl)phenyl)-9H-fluoren-2- amine (CAS 1613079-70-1) was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm.
  • the hole blocking layer is formed with a thickness of 5 nm by depositing 2-(3'-(9,9- dimethyl-9H-fluoren-2-yl)-[l,l'-biphenyl]-3-yl)-4,6-diphenyl-l,3,5-triazine on the emission layer.
  • the electron transporting layer (ETL) having a thickness of 31 nm is formed on the hole blocking layer by depositing 50 wt.-% 4'-(4-(4-(4,6-diphenyl-l,3,5-triazin-2- yl)phenyl)naphthalen-l-yl)-[l,l'-biphenyl]-4-carbonitrile and 50 wt.-% LiQ.
  • Yb was evaporated at a rate of 0.01 to 1 A/s at 10' 7 mbar to form an electron injection layer with a thickness of 2 nm on the electron transporting layer.
  • Ag/Mg (90: 10 vol%) is evaporated at a rate of 0.01 to 1 A/s at 10' 7 mbar to form a cathode with a thickness of 13 nm.
  • N-( ⁇ [l,l-‘biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)- 9H-fluoren-2-amine ⁇ was vacuum deposited on the cathode layer to form a capping layer with a thickness of 75 nm.
  • the OLED stack is protected from ambient conditions by encapsulation of the device with a glass slide. Thereby, a cavity is formed, which includes a getter material for further protection.
  • the current efficiency is measured at 20°C.
  • the current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between 0V and 10V.
  • the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd/m 2 using an Instrument Systems CAS-140CT too array spectrometer (calibrated by Deutsche Ak relie für sstelle (DAkkS)) for each of the voltage values.
  • the cd/A efficiency at 15 mA/cm 2 is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.
  • the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE).
  • EQE percent external quantum efficiency
  • the emission In top emission devices, the emission is forward directed, non-Lambertian and also highly dependent on the micro-cavity. Therefore, the efficiency EQE will be higher compared to bottom emission devices.
  • To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA/cm 2 .
  • Lifetime LT of the device is measured at ambient conditions (20°C) and 30 mA/cm 2 , using a Keithley 2400 sourcemeter, and recorded in hours.
  • the brightness of the device is measured using a calibrated photo diode.
  • the lifetime LT is defined as the time till the brightness of the device is reduced to 97 % of its initial value.
  • the increase in operating voltage AU is used as a measure of the operational voltage stability of the device.
  • This increase is also determined during the LT measurement and by subtracting the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 100 hours.
  • Table 3 shows the setup and performance of several comparative (C-l to C-5) and inventive examples (1-1 to 1-20).
  • N-( ⁇ [l,l-‘biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl- 9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine ⁇ was used as p-HIL hole transport matrix compound, except for C-4 and C-5 where it was CuPC:
  • the chemical formula of compound CR1 is as follows:
  • All inventive devices exhibit a lower operational voltage and at the same time a current efficiency in consideration of the cavity CIEY higher than the comparative devices.
  • the comparative devices C-l to C-3 contain WO3 as dopant in the hole injection layer (HIL) and an organic p-dopant BRI in the p-type charge generation layer (p-CGL).
  • HIL hole injection layer
  • p-CGL organic p-dopant BRI in the p-type charge generation layer
  • the comparative devices C-4 and C-5 contain CuPC and CNHAT in the HIL and an organic p-dopant BRI in the p-CGL.
  • the comparative device C-6 contains a metal compound M19 in the HIL and a metal compound M19 in the p-CGL.
  • the comparative device did not work, i.e. it does not emit light.
  • the comparative device C-7 contains a metal compound M18 in the HIL and a metal compound M18 in the p-CGL.
  • the comparative device did not work, i.e. it does not emit light.
  • the comparative device C-8 contains an organic p-dopant CR1 in the HIL and a metal compound M18 in the p-CGL.
  • the comparative device did not work, i.e. it does not emit light.
  • the comparative device C-9 contains an organic p-dopant CR1 in the HIL and an organic p-dopant BRI in the p-CGL.
  • the inventive devices 1-1 to 1-5 contain a metal compound in the HIL and an organic p-dopant BRI in the p-CGL.
  • the inventive devices 1-6 to 20 contain a metal compound in the HIL and an organic p-dopant BRI to Br5, respectively in the p-CGL.
  • the inventive device 1-21 contains a metal compound M18 in the HIL and an organic p-dopant BRI in the p-CGL.
  • Comparative devices C-8 and C-9 both contain an organic p-dopant in the HIL in contrast to the present invention. Moreover, comparative device C-9 differs from C-8 in that it contains an organic p-dopant BRI instead of a metal compound M18. It is apparent from this comparison that using only an organic p-dopant in the p-CGL is not sufficient in order to achieve a high efficiency as demonstrated for the inventive devices wherein a metal compound is used in the HIL and a radialene is the p-CGL.
  • the comparative devices C6 and C-7 represent devices of the prior art.
  • comparative device C-8 wherein an organic p-dopant is used in the HIL and a metal compound in the p-CGL, also do not even emit light.
  • a working OLED can only be produced by a certain combination of the HIL and p-CGL dopant and moreover, that the current efficiency can be remarkably increased.
  • Table 4 shows the setup and performance of these devices (all comparative, C6-C26).
  • N-( ⁇ [l,l-‘biphenyl]-4-yl)-9,9,dimethyl-N-(4-(9-phenyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine ⁇ was used as p-HIL hole transport matrix compound, except for C- 8 where it was CuPC.
  • Table 4 Setup and performance of several comparative single-stack devices.

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Abstract

La présente invention concerne un dispositif électroluminescent comprenant un composé de formule (I) et un composé de formule (II), et un dispositif d'affichage comprenant le dispositif électroluminescent organique.
EP23828126.5A 2022-12-13 2023-12-13 Dispositif électroluminescent organique comprenant un composé de formule (i) et un composé de formule (ii), et dispositif d'affichage comprenant le dispositif électroluminescent organique Pending EP4635273A1 (fr)

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EP22213037.9A EP4387415A1 (fr) 2022-12-13 2022-12-13 Dispositif électroluminescent organique comprenant un composé de formule (i) et un composé de formule (ii), et dispositif d'affichage comprenant le dispositif électroluminescent organique
PCT/EP2023/085693 WO2024126619A1 (fr) 2022-12-13 2023-12-13 Dispositif électroluminescent organique comprenant un composé de formule (i) et un composé de formule (ii), et dispositif d'affichage comprenant le dispositif électroluminescent organique

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EP23828126.5A Pending EP4635273A1 (fr) 2022-12-13 2023-12-13 Dispositif électroluminescent organique comprenant un composé de formule (i) et un composé de formule (ii), et dispositif d'affichage comprenant le dispositif électroluminescent organique

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EP4036080A1 (fr) * 2021-02-01 2022-08-03 Novaled GmbH Composé organique de formule (i) pour l'utilisation dans des dispositifs électroniques organiques, dispositif électronique organique comprenant ce composé et dispositif d'affichage comprenant le dispositif électronique organique
EP4002508A1 (fr) * 2020-11-16 2022-05-25 Novaled GmbH Dispositif électronique organique comprenant un composé de formule (1), dispositif d'affichage comprenant le dispositif électronique organique, ainsi que composés de formule (1) à utiliser dans des dispositifs électroniques organiques

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